Cetyl tranexamate mesylate (sold under the trade name TXVector) is a bioavailable derivative of

tranexamic acid Tranexamic acid is a medication used to treat or prevent excessive blood loss from major trauma, postpartum bleeding, surgery, tooth removal, nosebleeds, and heavy menstruation. It is also used for hereditary angioedema. It is taken eithe ...

for use in cosmetic formulations. Its primary use is in skincare products aimed at enhancing appearance by targeting

hyperpigmentation Hyperpigmentation, also known as the dark spots or circles on the skin, is the darkening of an area of Human skin, skin or nail (anatomy), nails caused by increased melanin. Causes Hyperpigmentation can be caused by sun damage, inflammation, or ...

, uneven skin tone, inflammation, dark spots, UV induced

erythema Erythema (, ) is redness of the skin or mucous membranes, caused by hyperemia (increased blood flow) in superficial capillaries. It occurs with any skin injury, infection, or inflammation. Examples of erythema not associated with pathology inc ...

, acne scars, and overall skin clarity.

Structure

Cetyl tranexamate mesylate is a lipophilic

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

and salt of the cyclic amino acid tranexamic acid. By esterification of the

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...

group on tranexamic acid, the molecule loses its

zwitterionic In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively and negatively charged functional groups. : (1,2-dipolar compounds, such as ylides, are sometimes excluded from t ...

structure, becomes positively charged with enhanced skin permeability. Its

lipophilic Lipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...

character and positive charge provide additional cosmetic benefits such as skin moisturization and powder-like feel. One unique aspect of cetyl tranexamate mesylate is that it is

cationic An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...

and has cationic

emulsification An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Although ...

capability. Therefore it is always formulated into cationic emulsions, which in some cases to be superior to anionic

emulsions An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Althoug ...

for skin health and moisturization.

Mechanism of action

Cetyl tranexamate mesylate is thought to act on the inflammatory pathway, reducing the

melanogenesis Melanocytes are melanin-producing neural crest-derived cells located in the bottom layer (the stratum basale) of the skin's epidermis, the middle layer of the eye (the uvea), the inner ear, vaginal epithelium, meninges, bones, and heart foun ...

and hyperpigmentation that is initiated by UV or acne inflammation. It differs from other hyperpigmentation actives, such as

hydroquinone Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para' ...

and

kojic acid Kojic acid is an organic compound with the formula . It is a derivative of 4-Pyrone, 4-pyrone that functions in nature as a chelation agent produced by several species of fungus, especially ''Aspergillus oryzae'', which has the Japanese common na ...

, which are toxic to melanocytes and thus lighten or bleach all skin to which they are applied. Cetyl tranexamate mesylate's selective targeting of inflamed

melanin Melanin (; ) is a family of biomolecules organized as oligomers or polymers, which among other functions provide the pigments of many organisms. Melanin pigments are produced in a specialized group of cells known as melanocytes. There are ...

production, such as post-inflammatory hyperpigmentation (PIH) and acne-induced hyperpigmentation (AIH), may explain its popularity with users having dark skin tone. For application on skin, cetyl tranexamate mesylate is substantially more bioavailable than unmodified tranexamic acid. The former permeates faster and diffuses to deeper layers of the skin, reaching live cells of the

stratum granulosum The stratum granulosum (or granular layer) is a thin layer of cells in the epidermis lying above the stratum spinosum and below the stratum corneum ( stratum lucidum on the soles and palms).James, William; Berger, Timothy; Elston, Dirk (2005) ''A ...

, whereas standard tranexamic acid does not.

Safety and regulation

Cetyl tranexamate mesylate is non-irritating and non-sensitizing in human studies. It is structural analogous to other lipophilic esters of amino acids which are readily biodegradable and non-toxic to the aquatic environment. Cetyl tranexamate mesylate is not on any country negative list for cosmetic products, though it is not yet approved as a skin brightening active under the China cosmetics regulation (CSAR).

References

{{reflist Cosmetics chemicals Amino acid derivatives Fatty acid esters